


The Dress-Up Bag

by reallygrossstuff



Category: Homestuck
Genre: Crossdressing, Curses, Diapers, Forced Crossdressing, Infantilism, Mental Regression, Transformation
Language: English
Status: Completed
Published: 2019-03-13
Updated: 2019-03-13
Packaged: 2019-11-16 16:15:47
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,869
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18097781
Author URL: https://archiveofourown.org/users/reallygrossstuff/pseuds/reallygrossstuff
Summary: Dave and Dirk go thrifting, and find some clothes with interesting attributes.





	The Dress-Up Bag

**Author's Note:**

> Another request from my Tumblr that I absolutely loved. Hopefully I've done it justice.

Thrifting was a long-practiced tradition among the Strider family. Hardly a weekend went by without one pair – or occasionally all three – going out at some point to scout some local charity shop or yard sale. As well as being a good bonding activity, it was a great way to supplement the Striders’ wardrobes, bookshelves and DVD collections – plus, it was just good fun.

This particular weekend’s thrift wasn’t particularly ambitious, but it was still shaping up to be an enjoyable waste of an afternoon. Dave and Dirk were milling about a little shop near their apartment, making pointless conversation and browsing idly through the assorted nick-knacks present.

“Find anything interesting yet?” Dirk leaned against the wooden bin as Dave continued to rifle through it.

“I did, but you didn’t agree with me.”

“Those hot pants were tacky and you knew it, I was doing you a favour by stopping you.”

“Excuse you, they were – wait, hang on, what’s this…?”

Dave trailed off as he rooted around in the tub, coming up with a fabric clothes bag, zipped shut. Overcome by curiosity, he unzipped it immediately, revealing a trove of casual clothing that seemed to be in much better condition than anything else they’d found.

“Aw hell yeah, check this out.” Dave grinned, pulling a baggy hoodie from amidst the clothes. “This is perfect.”

“It’s pink.” Dirk noted idly as he leaned closer to examine the collection himself.

“The _stitches_ are pink, I can deal with that.” He shook the pink-threaded garment out, dislodging a small amount of dust and lint from the surface of the mostly-black hoodie.

“Hm.” Dirk picked out some things for himself, finding a plain button-down and some shorts that seemed like they’d fit him well. “Wanna try some of this stuff on?”

“You know I do, bro.” Dave grabbed a heap of things for himself, walking with Dirk towards the shop’s changing stalls. Splitting into different stalls, they set about changing into their chosen outfits.

Leaving his own clothes in a pile, Dirk put on the clothes he’d gathered, surprised to find they were just his size. The crisp white shirt seemed almost tailored to fit him, and the shorts cut off perfectly halfway to his knees. Straightening it all a little and taking a moment to admire himself in the mirror, Dirk left the stall to get his brother’s opinion – and to offer his own.

Stepping out, he found Dave already dressed in his own outfit – relatively simpler, with the oversized hoodie and a pair of pale sweatpants. The siblings took a few moments to size each other up, examining each other’s clothing of choice before eventually Dirk couldn’t suppress a slight chuckle.

“You look ridiculous?”

“What? I look fine, you’re the one in a half-assed sailor costume.”

“You don’t look like anything, you’re just dressed for bed.”

“I look _good_ , thank you very much.” Dave crossed his arms defensively, face still devoid of expression behind his shades.

“Whatever.” Dirk shrugged, turning back to the full-length mirror placed in front of them. Leaning closer, though, he couldn’t help but notice something strange about his brother’s outfit. “Yo, bro, what’s with the ribbons?”

“…ribbons?” Dave leaned closer to the mirror, frowning at the pair of pink ribbons tied into his hair. “I didn’t put those there… were, uh. Were you wearing those socks before?”

“What?” When Dirk looked back at his own reflection, he found that his legs were hugged by a pair of long white socks where previously they’d been bare. “What the fuck…?”

“Uh, Dirk?”

In the time Dirk had been looking at himself, another change had overtaken Dave. What had previously been small pink stitches on his hoodie was spreading, the whole surface gradually turning bright pink – and on top of that, it seemed to be changing shape in some way.

Before Dirk could comment on that, or try to help, he was startled by a change to his own clothes. What had previously been a plain white outfit was now growing splotches of dark blue, forming patterns and accents along his body. Stripes began to form at the sleeves and collar of his shirt, along with a thick straight line to delineate the breast pocket. He noticed the same happening to his shorts, but forced himself to look away when the legs began to merge together, worried for what he’d end up seeing.

Turning his attention back to Dave, what Dirk saw was definitely cause for alarm. His sweatpants had shrunk and split, turning the same shade of pink as his top as they shifted into a pair of thigh-highs. The hoodie had transformed dramatically, both thinning and shrinking as it turned fully pink. Its sleeves had pulled upwards, puffing out around Dave’s shoulders with a slight lace trim – the same trim that circled the hem of what was undeniably some sort of flimsy princess dress. The whole ensemble was entirely off-brand for the ‘coolkid’, and even his suave façade was starting to crack under the pressure of so much embarrassment. To top it off, the short skirt of his dress was less than adequate in covering his underwear – and while Dirk didn’t keep a close eye on the sort of undergarments his brother wore, he was confident that the fluffy white padding and ruffled plastic pants were not part of his usual ensemble.

“Why are you wearing a diaper, Dave.” Dirk deadpanned, more just to say something than to make any criticism.

Dave crossed his arms petulantly, refusing to look at either Dirk or his own reflection. “Why are _you_ wearing a diaper.”

“…what? Oh.” Looking down at himself, Dirk realised that an identical garment was secured around his own waist, just peeking out under his new short skirt. With his ‘new’ clothes and the infantile underwear, Dirk looked like an overgrown toddler dressed in a sailor costume to match Dave’s princess. Just thinking about how the two of them looked brought heat to his cheeks, and that was before he saw a store attendant turning the corner to check on them.

As she laid her eyes on the pair, Dirk braced himself for nothing but the most derisive scorn – with the way they were dressed, they honestly deserved it – but she only put on a kind smile, stepping closer. “And do you two cuties need help with anything?”

“Um…” Dirk was honestly thrown by the nonchalance with which she addressed them. He was vaguely aware of Dave shielding himself behind his brother, pointlessly trying to avoid being seen. “No, we’re just… we’re gonna leave now.”

“Okay then. Do you need help finding your mommy or daddy?”

What was she talking about? They’d come in alone, and Dirk knew she’d seen that. “No, we’re fine. C’mon, bro.”

Trusting Dave to follow his lead, Dirk pressed forward and began to leave, trying not to get too flustered as he strode past the woman. Of course, they got past without incident, and both Striders attempted to salvage their composure, even as every step elicited obvious crinkling noises from their exposed padding.

They’d caught the bus to get to the store, but Dirk didn’t feel comfortable staying still, so it was a brisk walk through the neighbourhood to get home. Even that was made more difficult – or at least more awkward – as with every step he could feel the minute swish of his new skirt, and he was aware that every slight movement was only exposing his diaper more.

Strangely, though, nobody was reaction to that – at least in the way he’d expected. The first time someone’s stare lingered on him and his brother, instead of a jab or insult, they’d been greeted with a coo of adoration, even a well-meaning compliment. It might not have been as cruel as what he’d expected, but it still brought colour to his cheeks, and after a few more comments along those lines he couldn’t blame Dave for gripping his arm tight and trying to hide behind him in earnest.

“Dirk…” The older Strider was surprised to hear a slight whine in Dave’s voice as he mumbled. “How much longer do we gotta walk?”

Looking back and down at his brother, Dirk took in just what a sight Dave was. Not only did his outfit strip away any semblance of maturity he could muster, but the boy himself seemed to have none to give. His face was an open book, showing clearly the embarrassment and shyness he felt as he waddled along in his pink ensemble, his ruffled backside clearly visible to the world.

“Not too much longer, bro, promise.” Dirk felt the need to reassure him, though he was also more than a little worried. Sure it wasn’t the best situation to be in, but Dave would never act like this. He might not have had the best poker face in the Strider family, but he was still damn good at hiding things normally, so what was happening now?

Dave’s strange behaviour didn’t cease as they kept walking, and in fact only worsened as he got more and more attention for his outfit. As they entered their apartment building and climbed the stairs, the younger blonde kept a vice-like grip on Dirk’s arm, head turned downwards and cheeks aglow with blush. That posture only relaxed slightly when they got through their door, though he was at least comfortable enough to loosen his grip and let Dirk step away.

Before either of them could really start to decompress, Bro was out of his own room to greet them. Dirk tried to pre-empt any comment or concern, but was ignored as the eldest Strider talked over him.

“Hey there, kiddos. You two have fun?” Dirk just stared incredulously, but Dave answered with a glum shake of his head. “Aw, that’s too bad. Well, you’re home now, everything’s fine here. Need a change?” Again before Dirk could reply with indignance, Dave’s blush brightened as he made a small noise in his throat. Wait, had he actually…?

“That’s fine, kiddo, c’mere.” Holding his arms out, Dirk didn’t have a chance to confirm Dave’s state for himself before the pink-clad boy had wandered forward into his brother’s grip, from which he was promptly lifted up with only slight strain. “I’ll get you taken care of, then you can watch some TV, okay?”

“Okay…” Dave nodded, for some reason actually _relaxing_ as Bro cradled him like an infant. What was wrong with him?

As he bounced the boy in his arms, Bro turned his ( _extremely_ unusually) kind smile on the middle brother. “I can give you a change too, if you want. ‘Just in case’.”

Dirk was about to firmly refuse the offer, but a thought struck him – was he _sure_ he didn’t need a change? He hadn’t really been paying attention that, and if Dave needed one… he could easily check, but not without showing Bro that he wasn’t confident in himself. Taking the out, Dirk reluctantly nodded. “Okay. Just in case.”

As Bro carried Dave away to be ‘taken care of’, and Dirk followed for the same reason, he could only sigh at the strange situation he was in. It was certainly going to take some getting used to.

**Author's Note:**

> This was also posted to my Tumblr, [reallygrossstuff](https://reallygrossstuff.tumblr.com/).
> 
> I love the feedback these are getting, be sure to let me know what you think! And send a request through my Tumblr if you want to see something specific


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